CN113993875A - Organic electroluminescent compounds and organic electroluminescent devices using the same - Google Patents
Organic electroluminescent compounds and organic electroluminescent devices using the same Download PDFInfo
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- CN113993875A CN113993875A CN201980096647.XA CN201980096647A CN113993875A CN 113993875 A CN113993875 A CN 113993875A CN 201980096647 A CN201980096647 A CN 201980096647A CN 113993875 A CN113993875 A CN 113993875A
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Abstract
An organic electroluminescent compound and an organic electroluminescent device including the same are provided. By including the organic electroluminescent compound of the present disclosure, it is possible to provide an organic electroluminescent device having a lower operating voltage than that of a conventional organic electroluminescent device and thus achieving higher power efficiency.
Description
Technical Field
The present disclosure relates to an organic electroluminescent compound and an organic electroluminescent device comprising the same.
Background
An Electroluminescent (EL) device is a self-luminous device, which is advantageous in that it provides a wider viewing angle, a greater contrast ratio, and a faster response time. Organic EL devices were first developed by Eastman Kodak in 1987 by using small aromatic diamine molecules and aluminum complexes as materials for forming a light emitting layer [ appl. phys. lett. [ appphysics promo ]51,913,1987 ].
In Organic Light Emitting Diodes (OLEDs), low operating voltages are important to improve power efficiency. Specifically, the power efficiency of the OLED is obtained by [ (pi/voltage) × current efficiency ], and thus the power efficiency is inversely proportional to the voltage. That is, power efficiency can be improved by lowering the operating voltage of the OLED.
Meanwhile, korean patent application publication No. 2017-0022865 (published 3/2/2017) discloses an organic electroluminescent device using a phenanthrooxazole derivative as a red host. In addition, korean patent application laid-open No. 2017-0051198 (published 5/11/2017) discloses an organic electroluminescent device using a phenanthrooxazole derivative as an electron buffer layer or an electron transport layer. However, the above references do not specifically disclose anthracene-group containing compounds.
Disclosure of Invention
Problems to be solved
An object of the present disclosure is to provide an organic electroluminescent compound that efficiently generates an organic electroluminescent device having a lower operating voltage than that of a conventional organic electroluminescent device and thus realizes higher power efficiency.
Solution to the problem
Recently, in the OLED field, the red and green devices have successfully reduced the operating voltage, but the blue device still has an operating voltage about 0.5 to 1V higher than that of the red and green devices. Therefore, development to lower the operating voltage of the blue organic electroluminescent device is required.
The present inventors have recognized that an ETU (electron transfer unit) is required for the blue host to lower the operating voltage of the blue organic electroluminescent device. However, if the electron mobility is increased, the lifetime of the blue layer is gradually shortened. This is thought to be due to an increased electron attack on adjacent layers such as HTLs (hole transport layers). As a result of studies to solve the problems, the inventors of the present invention have found that the above object can be achieved by using a compound represented by the following formula 1, which has phenanthrene fused with ETU, as a blue host. Without wishing to be bound by theory, it is believed that phenanthrene has a stronger resonance than benzene or naphthalene, so that electrons can be more stable in phenanthrene. It is also believed that the compound represented by the following formula 1 may have better electron mobility and good electron stability by increasing resonance of ETU.
Wherein
X represents-N ═ -NR-, -O-, or-S-;
y represents-N ═ -NR-, -O-, or-S-; provided that one of X and Y represents-N ═ and the other of X and Y represents-NR-, -O-, or-S-;
r represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl; and is
R1To R9Each independently represents hydrogen, deuterium, halogen, cyano, or an alkyl groupSubstituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl; provided that R is1To R9At least one of them represents a substituted or unsubstituted anthracene group.
Effects of the invention
The organic electroluminescent device comprising the organic electroluminescent compound according to the present disclosure has a lower operating voltage than that of a conventional organic electroluminescent device, and thus can achieve higher power efficiency.
Detailed Description
Hereinafter, the present disclosure will be described in detail. However, the following description is intended to explain the disclosure and is not meant to limit the scope of the disclosure in any way.
The term "organic electroluminescent compound" in the present disclosure means a compound that can be used in an organic electroluminescent device and can be contained in any layer constituting the organic electroluminescent device if necessary.
The term "organic electroluminescent material" in the present disclosure means a material that may be used in an organic electroluminescent device and may include at least one compound. If necessary, the organic electroluminescent material may be contained in any layer constituting the organic electroluminescent device. For example, the organic electroluminescent material may be a hole injection material, a hole transport material, a hole assist material, a light emission assist material, an electron blocking material, a light emitting material (containing a host material and a dopant material), an electron buffering material, a hole blocking material, an electron transport material, an electron injection material, or the like.
Herein, the term "(C1-C30) alkyl" means a straight or branched chain alkyl group having 1 to 30 carbon atoms constituting the chain, wherein the number of carbon atoms is preferably 1 to 20, and more preferably 1 to 10. The above alkyl group may include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl and the like. The term "(C2-C30) alkenyl" means a straight or branched chain alkenyl group having 2 to 30 carbon atoms making up the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkenyl groups may includeIncluding ethenyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2-methylbut-2-enyl, and the like. The term "(C2-C30) alkynyl" means a straight or branched chain alkynyl group having 2 to 30 carbon atoms making up the chain, wherein the number of carbon atoms is preferably 2 to 20, and more preferably 2 to 10. The above alkynyl group may include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methylpent-2-ynyl and the like. The term "(C3-C30) cycloalkyl" means a monocyclic or polycyclic hydrocarbon having 3 to 30 ring backbone carbon atoms, wherein the number of carbon atoms is preferably 3 to 20, and more preferably 3 to 7. The cycloalkyl group may include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. The term "(3-to 7-membered) heterocycloalkyl" means a cycloalkyl group having 3 to 7, preferably 5 to 7 ring backbone atoms and containing at least one heteroatom selected from the group consisting of B, N, O, S, Si and P, and preferably consisting of O, S and N. The above-mentioned heterocycloalkyl group may include tetrahydrofuran, pyrrolidine, tetrahydrothiophene (thiolan), tetrahydropyran and the like. The term "(C6-C30) aryl" means a monocyclic or fused ring group derived from an aromatic hydrocarbon having 6 to 30 ring backbone carbon atoms, wherein the number of ring backbone carbon atoms is preferably 6 to 25, more preferably 6 to 18. The above aryl groups may be partially saturated and may contain a spiro structure. The above aryl group may include phenyl, biphenyl, terphenyl, naphthyl, binaphthyl, phenylnaphthyl, naphthylphenyl, phenylterphenyl, fluorenyl, phenylfluorenyl, benzofluorenyl, dibenzofluorenyl, phenanthryl, phenylphenanthryl, anthracenyl, indenyl, triphenylenyl, pyrenyl, tetracenyl, perylenyl, perylene, and the like,
Mesityl, naphthonaphthyl, fluoranthenyl, spirobifluorenyl, azulenyl, and the like. More specifically, the aryl group may include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, benzanthryl, 1-phenanthryl, 2-phenanthryl, 3-phenanthryl, 4-phenanthryl, 9-phenanthryl, naphthonaphthyl, pyrenyl, 1-
Base 2-
Base 3-
Base, 4-
Base 5-
Base 6-
Radical, benzo [ c]Phenanthryl, benzo [ g ]]
A group, a 1-triphenylene group, a 2-triphenylene group, a 3-triphenylene group, a 4-triphenylene group, a 1-fluorenyl group, a 2-fluorenyl group, a 3-fluorenyl group, a 4-fluorenyl group, a 9-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a 2-biphenyl group, a 3-biphenyl group, a 4-biphenyl group, an o-terphenyl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-quaterphenyl group, a 3-fluoranthyl group, a 4-fluoranthyl group, an 8-fluoranthyl group, a 9-fluoranthyl group, a benzofluoranthyl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a 2, 3-xylyl group, a 1-fluorenyl group, a 2-fluorenyl group, a 9-terphenyl group, a p-terphenyl group, a, 3, 4-xylyl group, 2, 5-xylyl group, mesityl group, o-cumyl group, m-cumyl group, p-tert-butylphenyl group, p- (2-phenylpropyl) phenyl group, 4' -methylbiphenyl group, 4' -tert-butyl-p-terphenyl-4-yl, 9-dimethyl-1-fluorenyl, 9-dimethyl-2-fluorenyl, 9-dimethyl-3-fluorenyl, 9-dimethyl-4-fluorenyl, 9-diphenyl-1-fluorenyl, 9-diphenyl-2-fluorenyl, 9-diphenyl-3-fluorenyl, 9-diphenyl-4-fluorenyl and the like.
Herein, the term "(5-to 30-membered) heteroaryl" means an aryl group having 5 to 30 ring backbone atoms and comprising at least one, preferably 1 to 4 heteroatoms selected from the group consisting of B, N, O, S, Si and P. The above-mentioned heteroaryl group may be a single ring, or a condensed ring condensed with at least one benzene ring; may be partially saturated; may be a heteroaryl group formed by linking at least one heteroaryl or aryl group to a heteroaryl group via one or more single bonds; and may comprise a spiro structure. The above heteroaryl group may include monocyclic heteroaryl groups such as furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, thiadiazolyl, isothiazolyl, isoxazolyl, oxazolyl, oxadiazolyl, triazinyl, tetrazinyl, triazolyl, tetrazolyl, furazanyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and the like; and fused-ring heteroaryl groups such as benzofuranyl, benzothienyl, isobenzofuranyl, dibenzofuranyl, dibenzothiophenyl, benzimidazolyl, benzothiazolyl, benzisothiazolyl, benzisoxazolyl, benzoxazolyl, isoindolyl, indolyl, benzindolyl, indazolyl, benzothiadiazolyl, quinolyl, isoquinolyl, cinnazinyl, quinazolinyl, benzoquinazolinyl, quinoxalyl, benzoquinoxalinyl, naphthyridinyl, carbazolyl, benzocarbazolyl, dibenzocarbazolyl, phenoxazinyl, phenothiazinyl, phenanthridinyl, benzodioxolyl, dihydroacridinyl and the like. More specifically, the heteroaryl group may include 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, pyrazinyl, 2-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 6-pyrimidinyl, 1,2, 3-triazin-4-yl, 1,2, 4-triazin-3-yl, 1,3, 5-triazin-2-yl, 1-imidazolyl, 2-imidazolyl, 1-pyrazolyl, 1-indolidinyl (indolidinyl), 2-indolidinyl, 3-indolidinyl, 5-indolidinyl, 6-indolidinyl, 7-indolidinyl, 8-indolidinyl, 2-imidazopyridinyl, 3-imidazopyridinyl, 5-imidazopyridinyl, 6-imidazopyridinyl, 7-imidazopyridinyl, 8-imidazopyridinyl, 3-pyridyl, 4-pyridyl, 1-indolyl, 2-indolyl, 3-indolyl, 4-indolyl, 5-indolyl, 6-indolyl, 7-indolyl, 1-isoindolyl, 2-isoindolyl, 3-isoindolyl, 4-isoindolyl, 5-isoindolyl, 6-isoindolyl, 7-isoindolyl, 2-furyl, 3-furyl, 2-benzofuryl, 3-benzofuryl, 4-benzofuryl, 5-benzofuryl, 6-benzofuryl, 7-benzofuryl, 1-isobenzofuryl, 3-isobenzofuryl, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group, 7-isobenzofuranyl group, 2-quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalyl group, 5-quinoxalyl group, 6-quinoxalyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, azacarbazolyl-1-yl group, azacarbazolyl-2-yl group, azacarbazolyl group, Azacarbazolyl-3-yl, azacarbazolyl-4-yl, azacarbazolyl-5-yl, azacarbazolyl-6-yl, azacarbazolyl-7-yl, azacarbazolyl-8-yl, azacarbazolyl-9-yl, 1-phenanthridinyl, 2-phenanthridinyl, 3-phenanthridinyl, 4-phenanthridinyl, 6-phenanthridinyl, 7-phenanthridinyl, 8-phenanthridinyl, 9-phenanthridinyl, 10-phenanthridinyl, 1-acridinyl, 2-acridinyl, 3-acridinyl, 4-acridinyl, 9-acridinyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-oxadiazolyl, 5-oxadiazolyl, 3-furazanyl, 2-thienyl, 3-thienyl, 2-methylpyrrol-1-yl, 2-methylpyrrol-3-yl, 2-methylpyrrol-4-yl, 2-methylpyrrol-5-yl, 3-methylpyrrol-1-yl, 3-methylpyrrol-2-yl, 3-methylpyrrol-4-yl, 3-methylpyrrol-5-yl, 2-tert-butylpyrrol-4-yl, 3- (2-phenylpropyl) pyrrol-1-yl, 2-methyl-1-indolyl, 4-methyl-1-indolyl, 2-methyl-3-indolyl, 4-methyl-3-indolyl, 2-tert-butyl-1-indolyl, 4-tert-butyl-1-indolyl, 2-tert-butyl-3-indolyl, 4-tert-butyl-3-indolyl, 1-dibenzofuranyl, 2-dibenzofuranyl, 3-dibenzofuranyl, 4-dibenzofuranyl, 1-dibenzothiophenyl, 2-dibenzothiophenyl, 3-dibenzothiophenyl, 4-dibenzothiophenyl, 1-silafluorenyl, 2-silafluorenyl, 3-silafluorenyl, 4-silafluorenyl, 1-germanium fluorenyl, 2-germanium fluorenyl, 3-germanium fluorenyl, 4-germanium fluorenyl, and the like. "halogen" includes F, Cl, Br and I.
Further, "ortho (o-)", "meta (m-)" and "para (p-)" are prefixes, and respectively indicate the relative positions of substituents. The ortho position means that two substituents are adjacent to each other, and for example when two substituents in a benzene derivative occupy positions 1 and 2, it is referred to as ortho position. Meta indicates that the two substituents are at positions 1 and 3, and is referred to as meta, for example, when the two substituents in the benzene derivative occupy positions 1 and 3. Para represents the two substituents at positions 1 and 4, and is referred to as para, for example, when the two substituents in the benzene derivative occupy positions 1 and 4.
In this context, "substituted" in the expression "substituted or unsubstituted" means that a hydrogen atom in a certain functional group is replaced by another atom or another functional group (i.e., substituent). In the present disclosure, the substituents of the substituted alkyl, substituted aryl, substituted heteroaryl and substituted anthracyl are each independently at least one selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (5-to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with a (5-to 30-membered) heteroaryl; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C6-C30) arylamino unsubstituted or substituted with (C1-C30) alkyl; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl. According to one embodiment of the present disclosure, each substituent is independently at least one selected from the group consisting of: (C1-C20) alkyl; (C6-C25) aryl unsubstituted or substituted with one or more (C1-C20) alkyl groups and/or one or more (5-to 25-membered) heteroaryl groups; and (5-to 25-membered) heteroaryl unsubstituted or substituted with one or more (C6-C25) aryl. According to another embodiment of the disclosure, each substituent is independently at least one selected from the group consisting of: (C1-C10) alkyl; (C6-C22) aryl unsubstituted or substituted with one or more (C1-C10) alkyl groups and/or one or more (5-to 18-membered) heteroaryl groups; and (5-to 20-membered) heteroaryl unsubstituted or substituted with one or more (C6-C18) aryl. For example, each substituent independently may be at least one selected from the group consisting of: methyl, phenyl, naphthylphenyl, phenyl substituted with one or more carbazolyl groups, naphthyl, phenylnaphthyl, biphenylnaphthyl, biphenyl, dimethylfluorenyl, phenanthryl unsubstituted or substituted with one or more phenyl groups, terphenyl, pyridyl substituted with one or more phenyl groups, pyrimidinyl substituted with one or more phenyl groups, benzofuranyl unsubstituted or substituted with one or more phenyl groups, quinolinyl substituted with one or more phenyl groups, quinazolinyl substituted with one or more phenyl groups, carbazolyl unsubstituted or substituted with one or more phenyl groups, dibenzofuranyl, dibenzothienyl, benzofurobenzofuranyl and naphthobenzofuranyl.
Herein, heteroaryl and heterocycloalkyl each independently may contain at least one heteroatom selected from B, N, O, S, Si and P. Further, the heteroatom may be bonded to at least one selected from the group consisting of: hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, substituted or unsubstituted (3-to 30-membered) heteroaryl, substituted or unsubstituted (C3-C30) cycloalkyl, substituted or unsubstituted (C1-C30) alkoxy, substituted or unsubstituted tri (C1-C30) alkylsilyl, substituted or unsubstituted di (C1-C30) alkyl (C6-C30) arylsilyl, substituted or unsubstituted (C1-C30) alkyldi (C6-C30) arylsilyl, substituted or unsubstituted tri (C6-C30) arylsilyl, substituted or unsubstituted mono-or di- (C1-C30) alkylamino, substituted or unsubstituted mono-or di- (C6-C30) arylamino, And substituted or unsubstituted (C1-C30) alkyl (C6-C30) arylamino.
In formula 1, X represents-N ═ NR-, -O-, or-S-; y represents-N ═ -NR-, -O-, or-S-; provided that one of X and Y represents-N ═ and the other of X and Y represents-NR-, -O-, or-S-. According to the disclosureIn one embodiment, one of X and Y represents-N ═ and the other of X and Y represents-O-or-S-. In the formula 1, the first and second groups,
respectively, represents a single bond or a double bond, depending on the chemical element bonded. For example, when X represents-N ═ bonded to X
Represents a double bond and, when X represents-O-, is bonded to X
Represents a single bond.
R represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl.
In formula 1, R1To R9Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl; provided that R is1To R9At least one of them represents a substituted or unsubstituted anthracene group. According to one embodiment of the present disclosure, R1To R9Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C25) aryl group; provided that R is1To R9At least one of them represents a substituted anthracene group. According to another embodiment of the disclosure, R1Represents a substituted or unsubstituted (C6-C18) aryl group, and R2To R9Each independently represents hydrogen, deuterium, or a substituted or unsubstituted (C6-C22) aryl group; provided that R is1To R9At least one of them represents a substituted anthracene group. For example, R1Represents phenyl or substituted anthracyl, and R2To R9Each independently represents hydrogen or a substituted anthracenyl group; provided that R is1To R9At least one of them represents a substituted anthracene group. Each substituent of the substituted anthracenyl group is independently at least one selected from the group consisting of: phenyl, phenyl,Naphthylphenyl, phenyl substituted with one or more carbazolyl groups, naphthyl, phenylnaphthyl, biphenylnaphthyl, biphenyl, dimethylfluorenyl, phenanthryl unsubstituted or substituted with one or more phenyl groups, terphenyl, pyridyl substituted with one or more phenyl groups, pyrimidinyl substituted with one or more phenyl groups, benzofuranyl unsubstituted or substituted with one or more phenyl groups, quinolinyl substituted with one or more phenyl groups, quinazolinyl substituted with one or more phenyl groups, carbazolyl unsubstituted or substituted with one or more phenyl groups, dibenzofuranyl, dibenzothiophenyl, benzofurobenzofuranyl and naphthobenzofuranyl.
Formula 1 may be represented by any one of the following formulae 1-1 to 1-9.
In the formulae 1-1 to 1-9, R1To R9X and Y are as defined in formula 1.
In the formulae 1-1 to 1-9, R11To R18Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl. For example, R11To R18Each independently represents hydrogen or deuterium.
In formulae 1-1 to 1-9, Ar represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group. According to one embodiment of the present disclosure, Ar represents a substituted or unsubstituted (C6-C25) aryl, or a substituted or unsubstituted (5-to 20-membered) heteroaryl. According to another embodiment of the present disclosure, Ar represents a (C6-C25) aryl group unsubstituted or substituted with at least one of one or more (C1-C10) alkyl groups, one or more (C6-C18) aryl groups, and a (5-to 20-membered) heteroaryl group; or a (5-to 20-membered) heteroaryl group unsubstituted or substituted with one or more (C6-C18) aryl groups. For example, Ar may represent phenyl, naphthylphenyl, phenyl substituted by one or more carbazolyl groups, naphthyl, phenylnaphthyl, biphenylnaphthyl, biphenyl, dimethylfluorenyl, phenanthryl unsubstituted or substituted by one or more phenyl groups, terphenyl, pyridyl substituted by one or more phenyl groups, pyrimidinyl substituted by one or more phenyl groups, benzofuranyl unsubstituted or substituted by one or more phenyl groups, quinolinyl substituted by one or more phenyl groups, quinazolinyl substituted by one or more phenyl groups, carbazolyl unsubstituted or substituted by one or more phenyl groups, dibenzofuranyl, dibenzothiophenyl, benzofurobenzofuranyl, or naphthobenzofuranyl.
The compound represented by formula 1 may be selected from the group consisting of the following compounds, but is not limited thereto.
In the above compounds, Dn represents n hydrogens that have been replaced by deuterium. For example, D1 to 25 indicates that 1 to 25 hydrogens have been replaced with deuterium.
The organic electroluminescent compounds according to the present disclosure can be prepared by synthetic methods known to those skilled in the art. For example, the organic electroluminescent compounds according to the present disclosure may be prepared by referring to the following reaction schemes 1 and 2, but are not limited thereto.
[ reaction scheme 1]
[ reaction scheme 2]
In schemes 1 and 2, Ar1And Ar2Either one of them represents a phenanthrooxazole derivative, and the other has the same definition as Ar described above.
Although illustrative synthetic examples of the compound represented by formula 1 are described above, those skilled in the art will readily understand that they are all based on the Buchwald-Hartwig cross-coupling reaction, the N-arylation reaction, the acidified montmorillonite (H-mont) -mediated etherification reaction, the Miyaura boronization reaction, the Suzuki (Suzuki) cross-coupling reaction, the intramolecular acid-induced cyclization reaction, the Pd (II) -catalyzed oxidative cyclization reaction, the Grignard reaction (Grignard reaction), the Heck reaction (Hereaction), the dehydration cyclization reaction, the SN reaction1Substitution reaction, SN2Substitution reaction, and phosphine-mediated reductive cyclization reaction, and the above reaction proceeds even if a substituent defined in the above formula 1 but not specified in a specific synthetic example is bonded.
Further, non-deuterated analogs of the compounds represented by formula 1 can be prepared by known coupling and substitution reactions. In addition, it can be prepared in a similar manner by using deuterated precursor materials, or more generally, can be prepared by treating non-deuterated compounds with deuterated solvents or D6-benzene in the presence of H/D exchange catalysts (such as lewis acids, for example, aluminum trichloride or ethyl aluminum chloride, triflic acid, or triflic acid-D).
The dopant that may be used in combination with the compounds of the present disclosure may be at least one phosphorescent or fluorescent dopant, preferably at least one phosphorescent dopant. The phosphorescent dopant is not particularly limited, but may be preferably selected from the group consisting of a metallized complex compound of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), more preferably an ortho-metallized complex compound selected from the group consisting of iridium (Ir), osmium (Os), copper (Cu), and platinum (Pt), and even more preferably an ortho-metallized iridium complex compound.
The compound represented by formula 1 of the present disclosure may be included in at least one layer constituting an organic electroluminescent device, and for example, in at least one layer selected from a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, a light emitting layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer. Each of the layers may additionally be composed of several layers. The compound represented by formula 1 of the present disclosure is not limited thereto, but may be included in the light emitting layer, and may be included in the light emitting layer as a host material.
The organic electroluminescent material of the present disclosure, for example, at least one of a hole injection material, a hole transport material, a hole auxiliary material, a light emission auxiliary material, an electron blocking material, a light emitting material, an electron buffering material, a hole blocking material, an electron transport material, and an electron injection layer, may include the compound represented by formula 1. The material may be a luminescent material. The light emitting material may be composed of only the compound represented by formula 1, and may further include one or more conventional materials included in the organic electroluminescent material. When two or more materials are contained in one layer, mixed deposition may be performed to form a layer, or co-deposition may be performed separately to form a layer.
An organic electroluminescent device according to the present disclosure includes a first electrode, a second electrode, and at least one organic layer between the first electrode and the second electrode. One of the first electrode and the second electrode may be an anode, and the other may be a cathode. The organic layer may include at least one light emitting layer, and may further include at least one layer selected from the group consisting of: a hole injection layer, a hole transport layer, a hole assist layer, a light emission assist layer, an electron transport layer, an electron buffer layer, an electron injection layer, an intermediate layer, a hole blocking layer, and an electron blocking layer.
The first electrode and the second electrode may each be formed of a transmissive conductive material, a transflective conductive material, or a reflective conductive material. The organic electroluminescent device may be a top emission type, a bottom emission type, or a both-side emission type according to the kind of materials forming the first electrode and the second electrode. In addition, the hole injection layer may be further doped with a p-type dopant, and the electron injection layer may be further doped with an n-type dopant.
The organic electroluminescent device of the present disclosure may include the compound represented by formula 1, and may further include one or more conventional materials included in the organic electroluminescent device. The organic electroluminescent device comprising the organic electroluminescent compound represented by formula 1 of the present disclosure may exhibit low operating voltage characteristics.
In addition, the organic electroluminescent material according to one embodiment of the present disclosure may be used as a light emitting material for a blue organic electroluminescent device. The organic electroluminescent material according to one embodiment of the present disclosure may also be applied to an organic electroluminescent device including QDs (quantum dots).
The present disclosure may provide a display system by using the compound represented by formula 1. Further, a display system or a lighting system can be produced by using the compound of the present disclosure. In particular, display systems, such as display systems for smartphones, tablets, laptops, PCs, TVs or cars, may be produced by using the compounds of the present disclosure; or a lighting system, such as an outdoor or indoor lighting system.
Hereinafter, the preparation method of the compound according to the present disclosure and the characteristics thereof will be explained in detail. However, the present disclosure is not limited to the following examples.
Example 1: preparation of Compound H-43
Synthesis of Compound 1-2
1.21g of Pd (PPh)3)2Cl2(1.72mmol), 19.8g of K2CO3(143.5mmol), 7g of phenylboronic acid (57mmol) and 19.27g of 9, 10-dibromoanthracene (57.41mmol) are added to 100mL of tetrahydrofuran, 100mL of distilled water and 100mL of toluene, and the mixture is stirred under nitrogen at 70 ℃ for 12 hours. After completion of the reaction, the aqueous layer was removed, and the organic layer was distilled under reduced pressure. The resulting mixture was separated by column chromatography to obtain 11.68g of Compound 1-2 (yield: 61.5%).
Synthesis of Compounds 1-3
1.264g of Pd2(dba)3(1.38mmol), 1.133g s-phos (2.76mmol), 10.16g KOAc (103.52mmol), 11.38g Compound 1-1(34.51mmol), and 10.514g bis (pinacolato) diboron (41.41mmol) were added to 250mL dioxane, and the mixture was stirred under nitrogen at 100 ℃ for 12 hours. After the reaction was completed, distilled water was added. The resulting solid was filtered. The resulting solid was separated by column chromatography to obtain 13g of the compounds 1 to 3 (yield: 89.4%).
Synthesis of Compound H-43
1.462g of Pd2(dba)3(1.60mmol), 1.31g of s-phos (3.19mmol), 16.92g of K3PO4(79.81mmol), 10.74g of Compound 1-2(32.24mmol) and 13.45g of Compound 1-3(31.92mmol) were added to 100mL of 1, 4-dioxane, 100mL of distilled water and 100mL of toluene, and the mixture was stirred at 100 ℃ for 12 hours under nitrogen. After completion of the reaction, the aqueous layer was removed, and the organic layer was distilled under reduced pressure. The resulting solid was separated by column chromatography to obtain 15.7g of Compound H-43 (yield: 89.9%).
| MW | Melting Point |
| 547.6 | 332℃ |
Example 2: synthesis of Compound H-1
In a reaction vessel, 7.6g of Compound 2-1(25.5mmol), 6g of Compound 2-2(18.2mmol), 0.4g of Pd (OAc)2(1.8mmol), 1.47g of s-phos (3.6mmol) and 3.49g of NaOt-bu (36.4mmol) were added to 250mL of toluene and the mixture was stirred at reflux. After 2 hours, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The organic layer was washed with distilled water. The obtained organic layer was distilled under reduced pressure, and the residue was separated by column chromatography (chlorobenzene: chloroform: 1:0 to 0:1) to obtain 8.7g of compound H-1 (yield: 87.4%).
| MW | Melting Point |
| 547.19 | 320.9℃ |
Example 3: synthesis of Compound H-29
In a reaction vessel, 5.1g of Compound 3-1(13.13mmol), 6g of Compound 3-2(18.2mmol), 0.4g of Pd (OAc)2(1.8mmol), 1.47g of s-phos (3.6mmol) and 3.49g of NaOt-bu (36.4mmol) were added to 250mL of toluene and the mixture was stirred at reflux. After 2 hours, the reaction mixture was cooled to room temperature and extracted with dichloromethane. The organic layer was washed with distilled water. The obtained organic layer was distilled under reduced pressure, and the residue was separated by column chromatography (chlorobenzene: chloroform: 1:0 to 0:1) to obtain 1.1g of compound H-29 (yield: 13.1%).
| MW | Melting Point |
| 637.74 | 358℃ |
Hereinafter, characteristics of the OLED including the compound according to the present disclosure will be explained. However, the following examples only illustrate the characteristics of the OLED according to the present disclosure in detail, but the present disclosure is not limited to the following examples.
Apparatus example 1: production of OLEDs using compounds according to the present disclosure
The organic electroluminescent compounds according to the present disclosure were used to produce OLEDs as follows: a transparent electrode Indium Tin Oxide (ITO) thin film (10 Ω/sq) (geomaoma co., ltd., Japan) on a glass substrate for an OLED was sequentially ultrasonically washed with acetone, ethanol, and distilled water, and then stored in isopropanol. Mounting an ITO substrate in a vacuum vapor deposition apparatusPreparing a substrate bracket. Introducing the compound HI-1 into a chamber of a vacuum vapor deposition apparatus, and then controlling the pressure in the chamber of the apparatus to 10-6And (4) supporting. Thereafter, a current was applied to the cell to evaporate the above-introduced material, thereby forming a first hole injection layer having a thickness of 60nm on the ITO substrate. Next, the compound HI-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole injection layer having a thickness of 5nm on the first hole injection layer. Then, the compound HT-1 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a first hole transport layer having a thickness of 20nm on the second hole injection layer. Then, the compound HT-2 was introduced into another cell of the vacuum vapor deposition apparatus, and the compound was evaporated by applying a current to the cell, thereby forming a second hole transport layer having a thickness of 5nm on the first hole transport layer. After forming the hole injection layer and the hole transport layer, a light emitting layer is formed thereon as follows: the compound H-43 was introduced into one chamber of the vacuum vapor deposition apparatus as a host, and the compound BD was introduced into the other chamber as a dopant. The two materials were evaporated and the dopant was deposited in a doping amount of 2 wt% based on the total amount of the host and the dopant to form a light emitting layer having a thickness of 20nm on the second hole transporting layer. Next, compound ET-1 and compound EI-1 were evaporated in two additional cells at a rate of 1:1 to deposit an electron transport layer having a thickness of 35nm on the light emitting layer. After the compound EI-1 was deposited as an electron injection layer having a thickness of 2nm on the electron transport layer, an Al cathode having a thickness of 80nm was deposited on the electron injection layer by another vacuum vapor deposition apparatus. Thus, an OLED was produced.
Apparatus example 2: production of OLEDs using compounds according to the present disclosure
An OLED was produced in the same manner as in device example 1, except that the compound H-1 was used as a host material of the light-emitting layer.
Comparative example 1: using conventional compoundsProduction of OLEDs
An OLED was produced in the same manner as in device example 1, except that compound BH-1 was used as a host material for the light-emitting layer.
Comparative example 2: production of OLEDs using conventional compounds
An OLED was produced in the same manner as in device example 1, except that the compound BH-2 was used as a host material for a light-emitting layer.
The compounds used in the apparatus examples and comparative examples are as follows.
The operating voltage, the light emitting efficiency, and the results of CIE color coordinates of the OLEDs produced in the device examples and the comparative examples at 1,000 nits luminance are shown in table 1 below.
[ Table 1]
From the above results, it was confirmed that the organic electroluminescent device including the compound having both the phenanthrooxazole structure and the anthracene-based structure as a host in the light emitting layer has an operating voltage lower than that of the conventional organic electroluminescent device. According to the present disclosure, a competitive operating voltage of the blue device (which may be comparable to that of the red and green devices) may be ensured to be applied to various applications such as a display.
Claims (7)
1. An organic electroluminescent compound represented by the following formula 1:
wherein
X represents-N ═ -NR-, -O-, or-S-;
y represents-N ═ -NR-, -O-, or-S-; provided that one of X and Y represents-N ═ and the other of X and Y represents-NR-, -O-, or-S-;
r represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl; and is
R1To R9Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl; provided that R is1To R9At least one of them represents a substituted or unsubstituted anthracene group.
2. The organic electroluminescent compound according to claim 1, wherein formula 1 is represented by any one of the following formulae 1-1 to 1-9:
wherein
R11To R18Each independently represents hydrogen, deuterium, halogen, cyano, substituted or unsubstituted (C1-C30) alkyl, substituted or unsubstituted (C6-C30) aryl, or substituted or unsubstituted (5-to 30-membered) heteroaryl;
ar represents a substituted or unsubstituted (C6-C30) aryl group, or a substituted or unsubstituted (5-to 30-membered) heteroaryl group; and is
R1To R9X and Y are as defined in claim 1.
3. The organic electroluminescent compound according to claim 1, wherein the substituent of the substituted alkyl group, the substituted aryl group, the substituted heteroaryl group, and the substituted anthracyl group is each independently at least one selected from the group consisting of: deuterium; halogen; a cyano group; a carboxyl group; a nitro group; a hydroxyl group; (C1-C30) alkyl; halo (C1-C30) alkyl; (C2-C30) alkenyl; (C2-C30) alkynyl; (C1-C30) alkoxy; (C1-C30) alkylthio; (C3-C30) cycloalkyl; (C3-C30) cycloalkenyl; (3-to 7-membered) heterocycloalkyl; (C6-C30) aryloxy; (C6-C30) arylthio; (5-to 30-membered) heteroaryl unsubstituted or substituted with (C6-C30) aryl; (C6-C30) aryl unsubstituted or substituted with a (5-to 30-membered) heteroaryl; a tri (C1-C30) alkylsilyl group; a tri (C6-C30) arylsilyl group; di (C1-C30) alkyl (C6-C30) arylsilyl; (C1-C30) alkyldi (C6-C30) arylsilyl; an amino group; mono-or di- (C1-C30) alkylamino; mono-or di- (C6-C30) arylamino unsubstituted or substituted with (C1-C30) alkyl; (C1-C30) alkyl (C6-C30) arylamino; (C1-C30) alkylcarbonyl; (C1-C30) alkoxycarbonyl; (C6-C30) arylcarbonyl; bis (C6-C30) arylboronyl; di (C1-C30) alkylborono carbonyl; (C1-C30) alkyl (C6-C30) arylboronyl; (C6-C30) aryl (C1-C30) alkyl; and (C1-C30) alkyl (C6-C30) aryl.
4. The organic electroluminescent compound according to claim 1, wherein the compound represented by formula 1 is any one selected from the group consisting of:
5. an organic electroluminescent material comprising the organic electroluminescent compound according to claim 1.
6. An organic electroluminescent device comprising the organic electroluminescent compound according to claim 1.
7. The organic electroluminescent device according to claim 6, wherein the organic electroluminescent compound is contained as a host material.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2019/087896 WO2020232655A1 (en) | 2019-05-22 | 2019-05-22 | Organic electroluminescent compound and organic electroluminescent device thereof |
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| CN202410073377.3A Division CN118047731A (en) | 2019-05-22 | Organic electroluminescent compounds and organic electroluminescent device using the same |
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| CN116283811A (en) * | 2021-09-15 | 2023-06-23 | 湖北尚赛光电材料有限公司 | Condensed ring compound and organic electroluminescent device thereof |
| CN113816909B (en) * | 2021-09-15 | 2023-07-11 | 武汉尚赛光电科技有限公司 | Organic electroluminescent material containing phenanthrene structure and device thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107922351A (en) * | 2015-08-19 | 2018-04-17 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and the Organnic electroluminescent device for including it |
| CN108137572A (en) * | 2015-10-30 | 2018-06-08 | 罗门哈斯电子材料韩国有限公司 | Electronics padded coaming, electron transport material and include its Organnic electroluminescent device |
| CN108329271A (en) * | 2018-04-04 | 2018-07-27 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device containing anthracene and benzimidazole structure |
| WO2018151470A1 (en) * | 2017-02-16 | 2018-08-23 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
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- 2019-05-22 CN CN201980096647.XA patent/CN113993875A/en active Pending
- 2019-05-22 KR KR1020217037237A patent/KR20220015383A/en active Search and Examination
- 2019-05-22 US US17/610,983 patent/US20220251051A1/en active Pending
- 2019-05-22 WO PCT/CN2019/087896 patent/WO2020232655A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107922351A (en) * | 2015-08-19 | 2018-04-17 | 罗门哈斯电子材料韩国有限公司 | Organic electroluminescent compounds and the Organnic electroluminescent device for including it |
| CN108137572A (en) * | 2015-10-30 | 2018-06-08 | 罗门哈斯电子材料韩国有限公司 | Electronics padded coaming, electron transport material and include its Organnic electroluminescent device |
| WO2018151470A1 (en) * | 2017-02-16 | 2018-08-23 | Rohm And Haas Electronic Materials Korea Ltd. | Organic electroluminescent compound and organic electroluminescent device comprising the same |
| CN108329271A (en) * | 2018-04-04 | 2018-07-27 | 长春海谱润斯科技有限公司 | A kind of electroluminescent organic material and its organic luminescent device containing anthracene and benzimidazole structure |
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| WO2020232655A1 (en) | 2020-11-26 |
| US20220251051A1 (en) | 2022-08-11 |
| KR20220015383A (en) | 2022-02-08 |
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